#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/49/2234915.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234915
loop_
_publ_author_name
'Singh, Durga Prasad'
'Pratap, Seema'
'Butcher, Ray J.'
'Gupta, Sushil K.'
_publ_section_title
;
 Methyl 2-(thiophene-2-carboxamido)benzoate
;
_journal_coeditor_code           BT5852
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1765
_journal_paper_doi               10.1107/S160053681202082X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H11 N O3 S'
_chemical_formula_moiety         'C13 H11 N O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29
_chemical_name_systematic
;
Methyl 2-(thiophene-2-carboxamido)benzoate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.2845(4)
_cell_length_b                   3.86753(8)
_cell_length_c                   15.6430(3)
_cell_measurement_reflns_used    1440
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      75.0507
_cell_measurement_theta_min      2.8225
_cell_volume                     1166.71(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Agilent Xcalibur Ruby Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2379
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         75.23
_diffrn_reflns_theta_min         4.59
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.573
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.4461
_exptl_crystal_size_mid          0.1795
_exptl_crystal_size_min          0.0394
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.270
_refine_ls_abs_structure_details 'Flack (1983), 206 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1422
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0597P)²+0.0898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                1381
_reflns_number_total             1422
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5852.cif
_cod_data_source_block           I
_cod_database_code               2234915
_cod_database_fobs_code          2234915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.25886(3) 0.20133(16) 0.72770(5) 0.03006(19) Uani d . 1 1
O O1 0.28253(10) 0.3657(6) 0.54680(14) 0.0304(4) Uani d . 1 1
O O2 0.51080(11) 0.8922(6) 0.60945(13) 0.0339(5) Uani d . 1 1
O O3 0.57519(10) 1.1406(5) 0.50816(14) 0.0308(4) Uani d . 1 1
N N1 0.38872(12) 0.6290(6) 0.56315(15) 0.0252(5) Uani d D 1 1
H H1B 0.4151(18) 0.698(9) 0.603(2) 0.037(10) Uiso d D 1 1
C C1 0.29286(16) 0.2186(7) 0.8287(2) 0.0307(6) Uani d . 1 1
H H1A 0.2694 0.1372 0.8781 0.037 Uiso calc R 1 1
C C2 0.35685(16) 0.3611(8) 0.8301(2) 0.0304(6) Uani d . 1 1
H H2A 0.3831 0.3919 0.8810 0.037 Uiso calc R 1 1
C C3 0.38110(14) 0.4607(7) 0.74725(17) 0.0249(5) Uani d . 1 1
H H3A 0.4251 0.5621 0.7364 0.030 Uiso calc R 1 1
C C4 0.33202(13) 0.3900(7) 0.68499(18) 0.0251(5) Uani d . 1 1
C C5 0.33132(14) 0.4577(7) 0.59160(18) 0.0247(6) Uani d . 1 1
C C6 0.40520(13) 0.7321(7) 0.4797(2) 0.0231(5) Uani d . 1 1
C C7 0.36094(14) 0.6720(7) 0.41074(19) 0.0262(6) Uani d . 1 1
H H7A 0.3173 0.5642 0.4201 0.031 Uiso calc R 1 1
C C8 0.38002(15) 0.7678(7) 0.3290(2) 0.0279(6) Uani d . 1 1
H H8A 0.3498 0.7185 0.2826 0.034 Uiso calc R 1 1
C C9 0.44255(15) 0.9352(7) 0.31331(18) 0.0277(6) Uani d . 1 1
H H9A 0.4550 1.0010 0.2569 0.033 Uiso calc R 1 1
C C10 0.48604(14) 1.0039(7) 0.38091(19) 0.0261(6) Uani d . 1 1
H H10A 0.5284 1.1221 0.3708 0.031 Uiso calc R 1 1
C C11 0.46910(13) 0.9032(7) 0.46454(18) 0.0241(6) Uani d . 1 1
C C12 0.51909(14) 0.9743(7) 0.53544(18) 0.0253(5) Uani d . 1 1
C C13 0.62744(16) 1.2115(9) 0.5729(2) 0.0359(7) Uani d . 1 1
H H13A 0.6645 1.3525 0.5479 0.054 Uiso calc R 1 1
H H13B 0.6469 0.9929 0.5937 0.054 Uiso calc R 1 1
H H13C 0.6062 1.3367 0.6206 0.054 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C4 91.59(15)
C12 O3 C13 115.6(3)
C5 N1 C6 128.7(2)
C5 N1 H1B 113(3)
C6 N1 H1B 117(3)
C2 C1 S1 112.4(2)
C2 C1 H1A 123.8
S1 C1 H1A 123.8
C1 C2 C3 113.2(3)
C1 C2 H2A 123.4
C3 C2 H2A 123.4
C4 C3 C2 111.1(2)
C4 C3 H3A 124.4
C2 C3 H3A 124.4
C3 C4 C5 131.5(2)
C3 C4 S1 111.7(2)
C5 C4 S1 116.7(2)
O1 C5 N1 125.2(3)
O1 C5 C4 121.2(3)
N1 C5 C4 113.5(2)
C7 C6 N1 122.3(2)
C7 C6 C11 118.6(3)
N1 C6 C11 119.1(3)
C8 C7 C6 120.6(3)
C8 C7 H7A 119.7
C6 C7 H7A 119.7
C7 C8 C9 121.3(3)
C7 C8 H8A 119.4
C9 C8 H8A 119.4
C10 C9 C8 118.9(3)
C10 C9 H9A 120.6
C8 C9 H9A 120.6
C9 C10 C11 121.4(2)
C9 C10 H10A 119.3
C11 C10 H10A 119.3
C10 C11 C6 119.2(2)
C10 C11 C12 119.4(2)
C6 C11 C12 121.4(3)
O2 C12 O3 122.8(3)
O2 C12 C11 125.2(3)
O3 C12 C11 112.1(2)
O3 C13 H13A 109.5
O3 C13 H13B 109.5
H13A C13 H13B 109.5
O3 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.711(3)
S1 C4 1.723(3)
O1 C5 1.226(3)
O2 C12 1.211(4)
O3 C12 1.329(3)
O3 C13 1.454(4)
N1 C5 1.365(4)
N1 C6 1.401(4)
N1 H1B 0.852(19)
C1 C2 1.352(4)
C1 H1A 0.9500
C2 C3 1.431(4)
C2 H2A 0.9500
C3 C4 1.385(4)
C3 H3A 0.9500
C4 C5 1.484(4)
C6 C7 1.395(4)
C6 C11 1.419(3)
C7 C8 1.381(4)
C7 H7A 0.9500
C8 C9 1.390(4)
C8 H8A 0.9500
C9 C10 1.375(4)
C9 H9A 0.9500
C10 C11 1.404(4)
C10 H10A 0.9500
C11 C12 1.495(4)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1B O2 . 0.852(19) 1.99(3) 2.665(3) 135(4)
C9 H9A O2 2_674 0.95 2.43 3.380(3) 174.2
C13 H13A O1 3_575 0.98 2.52 3.433(4) 154.3
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C4 S1 C1 C2 0.0(2)
S1 C1 C2 C3 -0.5(3)
C1 C2 C3 C4 0.8(4)
C2 C3 C4 C5 177.1(3)
C2 C3 C4 S1 -0.8(3)
C1 S1 C4 C3 0.4(2)
C1 S1 C4 C5 -177.8(2)
C6 N1 C5 O1 -0.8(5)
C6 N1 C5 C4 179.6(2)
C3 C4 C5 O1 178.3(3)
S1 C4 C5 O1 -3.9(4)
C3 C4 C5 N1 -2.1(4)
S1 C4 C5 N1 175.66(19)
C5 N1 C6 C7 1.1(4)
C5 N1 C6 C11 -178.8(3)
N1 C6 C7 C8 -177.9(3)
C11 C6 C7 C8 2.0(4)
C6 C7 C8 C9 -1.9(4)
C7 C8 C9 C10 0.3(4)
C8 C9 C10 C11 1.2(4)
C9 C10 C11 C6 -1.1(4)
C9 C10 C11 C12 178.1(2)
C7 C6 C11 C10 -0.5(4)
N1 C6 C11 C10 179.4(3)
C7 C6 C11 C12 -179.7(2)
N1 C6 C11 C12 0.2(4)
C13 O3 C12 O2 1.5(4)
C13 O3 C12 C11 -178.4(2)
C10 C11 C12 O2 -178.1(3)
C6 C11 C12 O2 1.0(4)
C10 C11 C12 O3 1.7(4)
C6 C11 C12 O3 -179.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 593984
